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I've been flirting with the idea of breaking out of corporate workplaces to moving into self employment.

The concerns I'm aware of are:

  • I need a sufficient financial buffer to survive spin-up and potential failures
  • My success depends entirely on my own efforts, if I get lazy, I will fail.
  • There is no guarantee of success
  • I will be responsible both financially and legally for anything I produce. Edit: I would seek legal consult to properly prepare for this

Concerns I have that I'm uncertain of:

  • How will breaking off on my own affect my career if I decide to come back to corporate workplaces?
  • If I did return to corporate work but maintained my successful projects on the side could it open me to complications in my career? Edit: assuming this work is not a conflict of interest or utilizing any work resources or time

Honestly my biggest concern is this... I've been VERY successful in my career thus far. (Primarily Software development / Some Project Management) If I were to go off on my own for say... Two years... how would that affect my employability if I then return to the Corporate Workplace?

To narrow the breadth this could cover let's just assume the business was profitable, just not as profitable as I had hoped and I decide I'd prefer to return to work in the corporate workplace instead.

  • Your known bullet 4 can (and really should) be mitigated by a corporation. Otherwise, I'm not sure this is answerable. Different people/companies will view self employment differently. – Telastyn Jul 3 '14 at 20:00
  • Yeah I'd probably set up an LLC or something. (likely taking to a lawyer first to know what's what) I also understand different companies would take this differently... I'm mostly curious "at large" would going off on my own to most companies be as if I paused my career, additional benefit, or backtracked... and what risks I might incur maintaining side projects post rehire. – RualStorge Jul 3 '14 at 20:07
  • For the second question, we'd really need to know more information about the type of work. Is any of this work related to the work being performed at the office? Do you have any contractual agreements with the corporate office? Was there any non-compete clause in your paperwork? Could the company accuse you of using company hours for your side project? – user17163 Jul 3 '14 at 20:09
  • @Thebluefish It would be software development stuff that would almost certainly not compete with the sort of jobs I pursue in the corporate world. (I edited the question) I would not use company resources or time, if any of my projects could conflict with the employer I'd agree to shut those down prior to starting. – RualStorge Jul 3 '14 at 20:13
  • For the last bullet, if your company has a moonlighting policy, you should check it out. – Ida Jul 3 '14 at 21:03
4

How will breaking off on my own affect my career if I decide to come back to corporate workplaces?

I've interviewed many previously self-employed folks for permanent positions. I've hired some, and rejected others.

When reading resumes and interviewing, my biggest concerns are:

  • Does this individual really want to be an employee, or an entrepreneur?
  • If the economy changes, will this person again decide that she/he wants to be self-employed and leave?
  • Is this person still working on the side, and if so will that distract from the work I need to get done?
  • Does this candidate want to join my company to learn about our systems/customers/market - so that he/she can leave later and compete with us?

Just having once been self-employed doesn't disqualify you from re-entering the corporate world, but you must be prepared to address these types of concerns that potential employers might have.

A side note: It's unfortunate that you are concerned about re-entering the corporate world before you have even left it. The most successful entrepreneurs I know are completely full of confidence in their own abilities to the extent that they don't have this worry. They were confident in their success. Think long and hard if you really want to be self-employed, or if your concern about re-entering the corporate world is just an expression of your doubt and an indication that perhaps you aren't yet ready for such a move.

  • +1: I like a lot of this answer (especially the side note). I think it misses some of the subtler changes that go into self-employment. – Joel Etherton Jul 8 '14 at 12:16
  • All the points on the resume/interview are good info, something to consider, but I feel I could mitigate concerns effectively, which is comforting. As far as planning to fail goes. In all business ventures I pursue be it a new jobs, investments, etc I set milestones and failure conditions. Essentially if/when I reach a milestone it's time for me to plan my next step (and set new milestones), if I hit a failure condition I pursue a plan of action to prevent further losses. (Never hit a failure condition yet, but I still plan accordingly) – RualStorge Jul 8 '14 at 14:29
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I really like the answer by @Joe Strazzere. It's pretty thorough from the standpoint of a future gaining employer. This answer is less a competing answer as much an "anecdotal supplement" to his.

I've been self-employed, and frankly it was awesome. I had terrific clients, really good work, and overall it was a terrific time for me. However, it did not survive a particularly calamitous national event at the time. There was nothing that could have prepared me for it, it just happened and that's life. Along that concept was never the idea that it would fail. I had made a decision to leave my employer and had no other job lined up, I simply decided (with encouragement from friends and clients) to start my own business. I never considered re-entering the work force. I never considered the possibility of it not lasting forever. An friend of mine who I refer to as a "serial entrepreneur" once told me: "If you plan for failure, you'll achieve it." So while it doesn't hurt to have some backup ideas, those safety nets will only hold you back in the end.

The real part that I don't @Joe Strazzere's answer doesn't cover is just what such a move can do for your actual skill set and experience. There are many "jobs" that go into maintaining a business, and as a self-employed individual you will be responsible for all of them. No matter what your field of expertise is in, you will not be doing that 100% of the time. Consider the effort it takes to maintain your skills in the job market today where that is your only focus. Now add bookkeeper, facilities maintainer, receptionist, scheduling clerk, and salesman on top of those skills. You will need to spend time doing all of these things at some point. I don't think you need to become an expert at these things, but the time they take up will detract from other things. Maybe you sacrifice family time, maybe you sacrifice your sleep schedule. Whatever it is, there simply isn't enough time in a day to do all of these things.

You can get away with "outsourcing" these things by hiring a receptionist or a CPA, etc., but in the end you will still find that over time your skills will morph from what they are today to more of a business acumen. This isn't a bad thing necessarily, but you have to consider if you plan to re-enter the corporate workforce afterward, will you still be relevant? I don't know your career field so I honestly couldn't say. I'm in software development, and with the time I lost not keeping those skills up to snuff I almost paced myself out of the industry in a single year.

When I did come back to the corporate world, the questions I faced regarded the decisions I made to go into business myself, why the business didn't succeed as I'd hoped, what I'd learned from it. In a couple of cases I was questioned on whether I could handle "working for someone else" again. Because my business was fairly short-lived (about a year), my work ethic and "tenacity" (for lack of a better term) were questioned. What interviewers really seemed to be going after was the idea that if I'd fail for me with everything on the line, what would convince them that I wouldn't fail for them with nothing of my own on the line.

I didn't have competing work when my business folded, but it was always in the back of the mind of the interviewer. There were always subtle questions about dedication, commitment and potential "distractions". There was always at least a casual mention of some corporate policy that forbids external work/jobs without approval or of a required non-compete agreement. I would recommend not having any such distractions when/if you return to a corporate gig as even the suggestion of competition or distraction will be a knock against you.

  • I agree, this actually won't be my first time running a business. I did so when I was younger (has it really already been a decade?) It was wildly successful to the point of burn out. At that age I simply was too inexperienced in hiring others so when I couldn't keep up with the volume of work I just burned myself out and passed the business off to a friend (Where he gave me a cut of the profit from the customers I handed him) It's amazing I did so well, I knew so little compared to now. – RualStorge Jul 8 '14 at 13:52
  • I have mixed feelings about the plan for failure point. If you're investing time in a failure plan, I agree. But you should plan for failure. My business I plan to pursue a number of projects. Many are smaller and likely "safe" trickle income. Others are more ambitious, but could land anywhere from wildly lucrative to never getting off the ground. You have to plan for at what point you consider a project a failure, and what to do when that happens. (in my case it's mothball it and move to the next one) This is how I see my business. I plan to succeed, but if I meet condition X pursue plan B. – RualStorge Jul 8 '14 at 14:54

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